1) Spent $40k on a skydiving trip to Virginia Beach/Norfolk at a military charity auction 4-5 months before I was laid off....
Took my husband, brother in law, sister, and dad on the trip last fall. Sister didn't jump but the rest of us did-my dad was 64 then and said it is the coolest thing he has ever done (and he has literally been all over the globe). Totally worth it. I was already FI when I bought the trip (tho I didn't fully realize it!), and I got to deduct over $30k of it from my taxes as a charitable donation, so that gave me a nice tax refund :). I probably wouldn't have bid for it had I thought my job was at risk, but I don't regret it (although I do sometimes think, 'could have bought another Detroit rental house for that wad of cash.'). Will likely never skydive again (it was SCARY, plus it's expensive & I can get more happiness bang for my bucks from aerial dance & my community pool), but I absolutely LOVED IT! Plus, it really helped with my fear of flying.
2) Had a flying trapeze and aerial dance addiction for ~7 years. $50/lesson for flying trap at 2 lessons/week-ended that 2 yrs ago because a neck injury (from bad ergonomics at my old job, not flying thru the air with he greatest of ease, natch) meant no more bouncing in the net. Then it was $35 aerial dance classes 2x/week....now I just pay to work out on the aerial apparatus at a circus school, they have open workout times and it's $17.50/workout. I try to go 1x/week (my amateur circus performing is on hold at the momentum, just trying to stay in climbing shape in case inspiration for a new routine strikes soon).
3) I'm too lazy to figure out how to quote, but for the pets comments, I'm there too! Probably have spent close to $15k on medical expenses for one of my dogs who has an autoimmune disorder. She's part of my family, it wasn't even a question. Worth EVERY penny! And then last fall (about 3 weeks after skydiving) we added to the family with a 'free' dog who promptly needed $800 worth of dental work. Totally worth it too!
We're not planning on having kids so any time dog stuff gets expensive, I repeat my mantra: 'it's cheaper than college...'